US2014024621A1PendingUtilityA1
Aminopyridine compounds and their uses
Est. expiryJul 23, 2032(~6 yrs left)· nominal 20-yr term from priority
C07D 213/74C07F 9/58C07D 405/12C07D 213/76A61P 25/00C07D 213/75C07D 213/72
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Claims
Abstract
The invention generally relates to aminopyridines and methods of use thereof. In certain embodiments, the invention provides an aminopyridine or a pharmaceutically-acceptable salt thereof, in which the aminopyridine or the salt thereof includes a cleavable functional group that substantially prevents extra-hepatic hydrolysis.
Claims
exact text as granted — not AI-modified1 . An aminopyridine or a pharmaceutically-acceptable salt thereof, wherein the aminopyridine is represented by formula (I):
wherein:
X 1 is selected from H, NH 2 , NHR 1 , N═NR 2 , N═R 3 , or NHCOOCH 3 ,
X 2 is selected from H, NH 2 , NHR 1 , N═NR 2 , or N═R 3 ,
X 3 is selected from NH 2 , NHR 1 , N═NR 2 , or N═CR 3 , wherein X 2 and X 3 are not both NH 2 ;
R 1 is selected from:
COR 4 , wherein R 4 is an amino acid attached at the carbonyl carbon;
COOR 5 , wherein R 5 is a C 2 or higher alkyl group;
COR 6 , wherein R 6 is a branched chain alkyl optionally substituted with a phenyl group, wherein the phenyl group is optionally substituted with a phosphonooxy group and optionally substituted with one or more alkyl groups;
a pyrone; and
SO 3 Na;
R 2 is a heterocycloalkenyl optionally substituted with one or more amino groups;
R 3 is a phenyl group optionally substituted with one or more halogens; or
R 3 is selected from the group consisting of formulas (II), (III), (IV), (V), (VI), (VII), (VIII), and (IX):
with the proviso that when X 3 is COOR 5 , R 5 is not an ethyl group, tert-butyl group, or n-dodecyl group.
2 . The aminopyridine of claim 1 , wherein R 4 is alanine, lysine, or phenylalanine.
3 . The aminopyridine of claim 2 , represented by a formula selected from the group consisting of (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), and (XVIII):
or a pharmaceutically acceptable salt thereof.
4 . The aminopyridine of claim 1 , represented by formula (XIX):
wherein R 5 is an n-propyl group; an n-butyl group; a sec-butyl group, or a straight or branched C 5 or higher alkyl chain, with the proviso that R 5 is not an n-dodecyl group;
or a pharmaceutically acceptable salt thereof.
5 . The aminopyridine of claim 1 , represented by a formula selected from the group consisting of (XX), (XXI), (XXII), and (XXIII):
wherein R 5 is a C 2 or higher alkyl group; or
or a pharmaceutically acceptable salt thereof.
6 . The aminopyridine of claim 5 , represented by formula (XXV):
or a pharmaceutically acceptable salt thereof.
7 . The aminopyridine of claim 5 , represented by formula (XXVI):
or a pharmaceutically acceptable salt thereof.
8 . The aminopyridine of claim 5 , represented by formula (XXVII):
or a pharmaceutically acceptable salt thereof.
9 . The aminopyridine of claim 5 , represented by formula (XXVIII):
or a pharmaceutically acceptable salt thereof.
10 . The aminopyridine of claim 1 , represented by the a formula selected from the group consisting of (XXIX), (XXX), and (XXXI):
wherein R 7 is a alkyl chain;
or a pharmaceutically acceptable salt thereof.
11 . The aminopyridine of claim 10 , wherein R 7 is a C 1 -C 6 straight or branched-chain alkyl.
12 . The aminopyridine of claim 1 , wherein R 6 is represented by formula (XXXII):
or a pharmaceutically acceptable salt thereof.
13 . The aminopyridine of claim 15 represented by the formula (XXXIII):
or a pharmaceutically acceptable salt thereof.
14 . The aminopyridine of claim 1 , wherein:
X 3 is NH 2 , X 1 is H, and X 2 is N═R 3 .
15 . The aminopyridine of claim 14 , represented by formula (XXXIV):
wherein X 4 is a halogen;
or a pharmaceutically acceptable salt thereof.
16 . The aminopyridine of claim 1 , represented by formula (XXXV):
or a pharmaceutically acceptable salt thereof.
17 . The aminopyridine of claim 1 , represented by formula (XXXVI):
or a pharmaceutically acceptable salt thereof.
18 . The aminopyridine of claim 1 , represented by formula (XXXVII):
or a pharmaceutically acceptable salt thereof.
19 . A method of treating a neural disorder, the method comprising administering an effective dose of an aminopyridine, or a pharmaceutically acceptable salt thereof, wherein the aminopyridine is represented by formula (I):
wherein:
X 1 is selected from H, NH 2 , NHR 1 , N═NR 2 , N═R 3 , or NHCOOCH 3 ,
X 2 is selected from H, NH 2 , NHR 1 , N═NR 2 , or N═R 3 ,
X 3 is selected from NH 2 , NHR 1 , N═NR 2 , or N═CR 3 , wherein X 2 and X 3 are not both NH 2 ;
R 1 is selected from:
COR 4 , wherein R 4 is an amino acid attached at the carbonyl carbon;
COOR 5 , wherein R 5 is a C 2 or higher alkyl group;
COR 6 , wherein R 6 is a branched chain alkyl optionally substituted with a phenyl group, wherein the phenyl group is optionally substituted with a phosphonooxy group and optionally substituted with one or more alkyl groups;
a pyrone; and
SO 3 Na;
R 2 is a heterocycloalkenyl optionally substituted with one or more amino groups;
R 3 is a phenyl group optionally substituted with one or more halogens; or
R 3 is selected from the group consisting of formulas (II), (III), (IV), (V), (VI), (VII), (VIII), and (IX):
with the proviso that when X 3 is COOR 5 , R 5 is not an ethyl group, tert-butyl group, or n-dodecyl group.
20 . The method of claim 19 , wherein R 4 is alanine, lysine, or phenylalanine.
21 . The method of claim 20 , wherein the aminopyridine is represented by a formula selected from the group consisting of (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), and (XVIII):
or a pharmaceutically acceptable salt thereof.
22 . The method of claim 19 , wherein the aminopyridine is represented by formula (XIX):
wherein R 5 is an n-propyl group; an n-butyl group; a sec-butyl group, or a straight or branched C 5 or higher alkyl chain, with the proviso that R 5 is not an n-dodecyl group;
or a pharmaceutically acceptable salt thereof.
23 . The method of claim 19 , wherein the aminopyridine is represented by a formula selected from the group consisting of (XX), (XXI), (XXII), and (XXIII):
wherein R 5 is a C 2 or higher alkyl group; or
a pharmaceutically acceptable salt thereof.
24 . The method of claim 23 , wherein the aminopyridine is represented by formula (XXV):
or a pharmaceutically acceptable salt thereof.
25 . The method of claim 23 , wherein the aminopyridine is represented by formula (XXVI):
or a pharmaceutically acceptable salt thereof.
26 . The method of claim 23 , wherein the aminopyridine is represented by formula (XXVII):
or a pharmaceutically acceptable salt thereof.
27 . The method of claim 23 , wherein the aminopyridine is represented by formula (XXVIII):
or a pharmaceutically acceptable salt thereof.
28 . The method of claim 19 , wherein the aminopyridine is represented by the a formula selected from the group consisting of (XXIX), (XXX), and (XXXI):
wherein R 7 is a alkyl chain;
or a pharmaceutically acceptable salt thereof.
29 . The method of claim 28 , wherein R 7 is a C 1 -C 6 straight or branched-chain alkyl.
30 . The method of claim 19 , wherein R 6 is represented by formula (XXXII):
or a pharmaceutically acceptable salt thereof.
31 . The method of claim 30 , wherein the aminopyridine is represented by the formula (XXXIII):
or a pharmaceutically acceptable salt thereof.
32 . The method of claim 19 , wherein:
X 3 is NH 2 , X 1 is H, and X 2 is N═R 3 .
33 . The method of claim 32 , wherein the aminopyridine is represented by formula (XXXIV):
wherein X 4 is a halogen;
or a pharmaceutically acceptable salt thereof.
34 . The method of claim 19 , wherein the aminopyridine is represented by formula (XXXV):
or a pharmaceutically acceptable salt thereof.
35 . The method of claim 19 , wherein the aminopyridine is represented by formula (XXXVI):
or a pharmaceutically acceptable salt thereof.
36 . The method of claim 19 , wherein the aminopyridine is represented by formula (XXXVII):
or a pharmaceutically acceptable salt thereof.Join the waitlist — get patent alerts
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